Holiday houses in Oakley

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Top-rated holiday rentals in Oakley

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A historic two-story home features a large front porch with white railings, surrounded by a well-maintained lawn and decorative flower planters. Tall trees provide shade, and a driveway leads to a two-car garage at the side.
Loft in Monticello
4.99 out of 5 average rating, 815 reviews

Monticello Carriage House

This carriage house is located at the back of the property of a 117-year-old historic home 4 blocks from downtown shopping and dining. We're 15 minutes from Allerton Park & Retreat Center, 25 minutes to Champaign and 30 minutes from Decatur. You’ll enjoy the comfy bed, two dining/game spaces, TV area, a small kitchen with cooktop, small refrigerator, microwave, coffee pot and a full bathroom. It is great for a weekend get-away! Come to enjoy Monticello! Same-day bookings-6:30 check-in time

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Guest favourite
Home in Decatur
4.93 out of 5 average rating, 28 reviews

Welcome to your home away from home!

Whether you’re here for work, relaxation, or a little of both, our thoughtfully designed space offers comfort, convenience, and plenty of room to unwind. Spacious 3BD/2BR home with new furniture, full kitchen, large living room, central A/C, free Wi-Fi, and on-site laundry. Off-street parking for 2 cars. Walk to Starbucks, Target, Olive Garden & 15 min from the airport. Flexible check-in/out and outdoor security cameras for peace of mind. Perfect for families, couples, or business travelers!

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Top Guest favourite
A renovated red caboose, TP&W 527, is positioned on railroad tracks surrounded by grass. The structure features white wheels and an elevated cupola, with windows and a yellow emblem. Green trees provide a natural backdrop, and a cobblestone pathway leads to the entrance.
Train in Oreana
4.99 out of 5 average rating, 159 reviews

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

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Superhost
The exterior of a charming cottage features a white facade with yellow awnings above the windows. A small porch is adorned with blue chairs and a yellow bicycle, complemented by a neatly manicured lawn and vibrant lavender flowers along the front edge.
Home in Decatur
4.83 out of 5 average rating, 355 reviews

Beach Vibes in the City | Family & Pet-Friendly

Soak up summer vacation vibes all year long at our breezy beach-themed cottage! 🌴 Fully fenced backyard is perfect for kids & fur babies to safely play. 3 minutes to Millikin University & Fairview Park 8 minutes to Memorial Hospital 15 minutes to Caterpillar & ADM Gas, groceries, and Walgreens are just around the corner. Check out family-owned local faves - Diamond's Family Restaurant & Krekel's Kustard Kick off your shoes and relax—you’ve found your home away from the shore! 🐚

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Top Guest favourite
Home in Decatur
5.0 out of 5 average rating, 30 reviews

Game Room Getaway 4BR 3BA w/ Pool Table in Decatur

Spacious 4BR/3BA Decatur brick home perfect for families or workers. Relax in open living areas, play a game on the pool table, or enjoy coffee from the stocked bar. A dedicated desk and fast Wi-Fi make remote work easy, while free parking out front keeps travel simple. Whether you’re gathering with family, traveling with colleagues, or needing a comfortable base during a work project, this Decatur stay offers the space, amenities, and welcoming atmosphere to make you feel at home.

LocationFamilyNearby

Superhost
A log cabin with a green metal roof is set amid a wooded backdrop. The front porch features wooden railings and multiple seating areas. Lush grass surrounds the cabin, enhancing its natural setting. A stone walkway leads to the entrance, creating an inviting access point.
Cabin in Decatur
4.84 out of 5 average rating, 93 reviews

Critter Cove

1350 N Country Club Critter Cove Nestled on 33 acres of Wooded wonderland in a country setting is the log cabin for you. Perfect for a getaway, family reunion, corporate retreat or even that upcoming wedding. The 4 bedroom and loft (5th bedroom) have single beds that can be pushed together to form king size beds. Perfectly nestled in the woods allowing you to become one with nature. Enjoy the peace and quiet and beautiful nature and wildlife views from your deck. Pet friendly!

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Guest favourite
Cottage in Decatur
4.89 out of 5 average rating, 149 reviews

Cozy Lakefront Retreat w/ Dock, Kayaks & Games

Welcome to Lake Shore Cottage, hosted by Beyond the Path Vacation Rentals, where your experience is our priority. Enjoy lakefront living: fish from the private dock, paddle kayaks, relax by the fire pit, and enjoy the peaceful waterfront views. Comfortable beds, fast Wi‑Fi, huge digital game board, smart TV, fully equipped kitchen, quiet safe neighborhood, minutes to Scovill Zoo, Devon Amphitheater, Nelson Park, Splash Cove, restaurants, shopping, and available boat rental.

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Guest favourite
A comfortable navy blue sofa is adorned with gold and blue decorative pillows. In front, a glass coffee table holds a gold bowl and blue candles. Wall art is featured above the sofa, framed in gold, complementing the contemporary decor.
Home in Decatur
5.0 out of 5 average rating, 19 reviews

My Home is Your Home

Stylish & Cozy Retreat / Great Location: Relax in this calm, modern space featuring a comfy leather sectional, ottoman, fireplace and 65' smart TV with all streaming services plus PPV. The open family/dining room seats four, and both bedrooms offer queen beds and 55' mounted TVs. Enjoy a quiet reading room, large kitchen and bath and washer and dryer. Outside, enjoy a large fenced-in yard. Centrally located near ADM, The Devon and Farm Progress Showgrounds

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Guest favourite
Home in Decatur
4.82 out of 5 average rating, 148 reviews

Lakefront Haven in Decatur

Escape to the peaceful shores of Lake Decatur at this beautifully updated lakefront retreat. Enjoy fishing, boating, or relaxing from your private dock, then unwind around the stunning fireplace or take in sunset views from the spacious deck. The open-concept layout offers inviting gathering spaces and plenty of room for families and friends to connect, relax, and enjoy the perfect lake getaway just minutes from local dining, parks, and attractions.

LocationFamilyPets

Top Guest favourite
The living room features a spacious sectional sofa in neutral tones, accompanied by a wooden coffee table. Natural light enters through the large windows, with light curtains framing the view. A ceiling fan is present, enhancing air circulation. Decorative art is displayed on the walls.
Home in Clinton
4.97 out of 5 average rating, 141 reviews

Upper Deck

Beautiful 3 bedroom home. Conveniently located on the edge of town, minutes from Clinton Lake and Historical downtown Clinton. Close to multiple restaurants, shopping and other entertainment options. The home has a well stocked kitchen with a charming dining room. There is also a large back deck with furniture and a grill. Plenty of on-premise parking. This is a second story home so there are stairs to access the property.

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Top Guest favourite
The entrance features a white door framed by blue and white siding. A welcome sign is prominently displayed beside the door, complemented by a potted plant at the base of the steps. Sunlight brightens the area, highlighting the welcoming ambiance.
Apartment in Arthur
4.98 out of 5 average rating, 314 reviews

The Hideaway - Charming apartment in Arthur IL

Enjoy exploring Illinois' largest Amish settlement while relaxing in this one-bedroom apartment one block from downtown Arthur, a village of 2200. Country charm abounds in this gem which sleeps three (full bed plus fold-out love seat). There is a private entrance, access to laundry facilities, and private parking off the street. We are 9 miles west of I-57 on Route 133 (take exit 203 at Arcola) and 40 miles from Champaign.

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Guest favourite
A charming home is captured from the front, featuring a blue exterior and a bright yellow garage door. Lush green grass surrounds the driveway, which is adorned with bricks. A small porch with steps leads to the entrance, framed by welcoming greenery.
Home in Decatur
4.89 out of 5 average rating, 205 reviews

Freshly remodeled lake area home

Enjoy your time at your home. Located across the street from Nelson Park, it is a short walk to the Devon Amphitheater, Splash Cove and mini golf around the corner. Plenty of restaurants or cook your own meals here. The docks to Lake Decatur and the Beach House restaurant are nearby also. Short drive to the hospitals.

LocationFamilyComfort

Popular amenities for Oakley holiday rentals